This thesis explores the reaction of primary amines with 1,2-dibromoethane and
1,3-dibromopropane as a one step synthesis of N,N"-disubstituted ethylenediamines, RNH-
CH2CH2-NH-R, N,N"-disubstituted propanediamines, R-NH-CH2CH2CH2-NH-R and
N-substituted azetidines RN[(CH2)3]. Unlike earlier approaches in the literature, this
method circumvents the use of the highly toxic #-haloamines.
The reaction can also be a convenient approach to N,N",N""-trisubstituted
diethylenetriamines which form as byproducts in the synthesis of the ethylenediamines
and are readily separated by distillation. The respective propylenetriamines were
obtained in analogous fashion from 1,3-dibromopropane. The use of N,Nʼ,N”-
trisubstituted triamines for the stabilization of low valent main group compounds was
exemplified through the synthesis and structural characterization of a phosphenium salt.
N,N'-disubstituted ethylenediamines, R-NH-CH2CH2-NH-R" bearing different
substituents R are difficult to obtain and require multi-step protocols. This thesis
describes their one step synthesis from aziridines and primary amines. The analogous
1,3-propandiamines were obtained from primary amines and azetidines.
N-tert-Butylimidazol was obtained through thermolysis of 1,3-di-tertbutylimidazolium
chloride and used as precursor for bis carbenes.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:OGU.10214/3148 |
| Date | 23 November 2011 |
| Creators | Krause, Michael |
| Contributors | Denk, Michael |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Thesis |
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